CN106118631A - A kind of preparation method of pure organic room temperature phosphorimetry polymeric material - Google Patents
A kind of preparation method of pure organic room temperature phosphorimetry polymeric material Download PDFInfo
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- CN106118631A CN106118631A CN201610428357.9A CN201610428357A CN106118631A CN 106118631 A CN106118631 A CN 106118631A CN 201610428357 A CN201610428357 A CN 201610428357A CN 106118631 A CN106118631 A CN 106118631A
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- room temperature
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- pure organic
- temperature phosphorimetry
- acrylamide
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- BRVSJSWXWXIMDT-ATPLWMGHSA-N C/C=C\[C@@H]1C=C(C)CCC1 Chemical compound C/C=C\[C@@H]1C=C(C)CCC1 BRVSJSWXWXIMDT-ATPLWMGHSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1475—Heterocyclic containing nitrogen and oxygen as heteroatoms
Abstract
The present invention relates to the preparation method of a kind of pure organic room temperature phosphorimetry polymer, belong to luminous organic material field.The method is applicable to the aromatic rings phosphorescent monomer of major part band bromine, by copolymerization simple with acrylamide, has obtained the pure organic polymer material with the room temperature phosphorimetry characteristics of luminescence.The present invention does not use the heavy metal of costliness, and raw material is simple and easy to get, and preparation method is easy, and obtained material emission function admirable, water-soluble and nontoxic, can apply to a lot of field.
Description
Technical field
The present invention relates to the preparation method of a kind of pure organic room temperature phosphorimetry polymeric material, belong to luminous organic material neck
Territory.
Background technology
Organic room temperature phosphorimetry material suffers from being widely applied at the aspect such as bio-imaging, chemical sensitisation, it is accordingly required in particular to have
The preparation method of a kind of simplicity and the course of processing.Current room temperature phosphor material is concentrated mainly on noble metal complexes aspect, and expensive
Metal cost intensive and be harmful to organism, therefore develops pure organic room temperature phosphorimetry material and seems and be highly desirable to.The purest have
Unit room temperature phosphor material is mainly crystalline state, and this needs strict condition of culture and process uncontrollable, and material is the most fragile, holds
Easily lose luminosity.
In order to overcome the shortcoming of the pure organic room temperature phosphorimetry material of crystalline state, the present invention is mainly by using pure organic room temperature phosphorimetry
Monomer and acrylamide copolymerization obtain room temperature phosphorimetry polymeric material, and obtain is unbodied powder, and post processing is simple.With often
Metal-organic complex compare, the present invention uses a purely organic system, reduces cost, and the product obtained is the most nontoxic,
Furthermore, it is possible to by the glow color of structure design regulation material, material has stronger room temperature under room temperature and amorphous state
The phosphorescence characteristics of luminescence, overcomes conventional crystalline material under amorphous state without room temperature phosphorimetry and the shortcoming of preparation difficulty, greatly promotes
The development of pure organic room temperature phosphorimetry material.
Summary of the invention
The shortcoming existed for prior art, the pure organic room temperature phosphorimetry that it is an object of the invention to provide a kind of simplicity gathers
The preparation method of laminate material.
Technical scheme: the preparation method of a kind of pure organic room temperature phosphorimetry polymeric material, with heavy atom
On the basis of the aromatic rings of group, by copolymerization simple with acrylamide, obtain that there is the pure of the room temperature phosphorimetry characteristics of luminescence
Organic polymer material；Specifically comprise the following steps that the preparation of (1) phosphorescent monomer；Basis at the aromatic rings with heavy atom group
On, the alkyl chain of one end band olefinic double bonds in modification, concrete structure (but being not limited to following structure) is as follows:
(2) preparation of phosphorescent monomer/acrylamide copolymer；
Phosphorescent monomer and acrylamide are dissolved in the organic solvent of 2 ~ 5 mL, wherein phosphorescent monomer and the mass ratio of acrylamide
Being 1:5 ~ 1:50, and add azodiisobutyronitrile as initiator, initiator amount is 1:8 ~ 1 with the mass ratio of phosphorescent monomer:
30, system deoxygenation 30 min, react 12 h at 65 DEG C.Products therefrom methanol washs, dried that pure organic room temperature phosphorimetry gathers
Laminate material.
In phosphorescent monomer in described step (1), the position of heavy atom, number and kind do not limit, the band olefinic double bonds connect
The length of alkyl chain does not limits, and the solvent in step (2) is DMF or dimethyl sulfoxide, and initiator is not limited to idol
Nitrogen bis-isobutyronitrile.
Compared with prior art, the present invention has a following significantly advantage:
The pure organic room temperature phosphorimetry polymer prepared by the present invention at room temperature has the strongest luminosity and is amorphous state,
Overcome the shortcoming that conventional pure organic room temperature phosphorimetry material can only be luminous under low temperature, deoxygenation or crystalline state；The product of amorphous powder
State, is beneficial to be processed further；Owing to there is no the participation of noble metal, greatly reduce cost；The preparation of phosphorescent monomer is simple, poly-
Conjunction process and post processing are the easiest；The polymer generated is water-soluble and nontoxic, is greatly expanded its application；Can be by changing
Different phosphorescent monomer regulates the position of emission peak to realize different purposes.
Specific embodiments
Below in conjunction with example, the present invention is described in detail:
Embodiment one:
The preparation method of a kind of pure organic room temperature phosphorimetry polymeric material, specifically comprises the following steps that
Weigh 0.050 g compound 1,0.545 g acrylamide, 0.0025 g azodiisobutyronitrile is dissolved in 2ml N, N-dimethyl
Methanamide, air-blowing deoxygenation 30 min, reacts 12 h at 65 DEG C.Products therefrom methanol washs, dried product.
Its quantum yield is 11.4%, and emission peak is at about 510 nm, and the life-span is 1.15 ms.
Embodiment two:
The preparation method of a kind of pure organic room temperature phosphorimetry polymeric material, specifically comprises the following steps that
Weigh 0.050 g compound 2,0.555 g acrylamide, 0.0026 g azodiisobutyronitrile is dissolved in 2ml N, N-dimethyl
Methanamide, air-blowing deoxygenation 30 min, reacts 12 h at 65 DEG C.Products therefrom methanol washs, dried product.
Its quantum yield is 8.1%, and emission peak is at about 520 nm, and the life-span is 5.76 ms.
Embodiment three:
The preparation method of a kind of pure organic room temperature phosphorimetry polymeric material, specifically comprises the following steps that
Weigh 0.050 g compound 3,0.443 g acrylamide, 0.0021 g azodiisobutyronitrile is dissolved in 2ml N, N-dimethyl
Methanamide, air-blowing deoxygenation 30 min, reacts 12 h at 65 DEG C.Products therefrom methanol washs, dried product.
Its quantum yield is 7.4%, and emission peak is at about 580 nm, and the life-span is 5.08 ms.
Claims (2)
1. the preparation method of a pure organic room temperature phosphorimetry polymeric material, it is characterised in that at the fragrance with heavy atom group
On the basis of ring, by copolymerization simple with acrylamide, obtain the pure organic polymer with the room temperature phosphorimetry characteristics of luminescence
Material；Specifically comprise the following steps that
(1) preparation of phosphorescent monomer；
On the basis of the aromatic rings with heavy atom group, the alkyl chain of one end band olefinic double bonds in modification；
(2) preparation of phosphorescent monomer/acrylamide copolymer；
Phosphorescent monomer and acrylamide are dissolved in the organic solvent of 2 ~ 5 mL, wherein phosphorescent monomer and the mass ratio of acrylamide
Being 1:5 ~ 1:50, and add azodiisobutyronitrile as initiator, initiator amount is 1:8 ~ 1 with the mass ratio of phosphorescent monomer:
30, system deoxygenation 30 min, react 12 h at 65 DEG C, and products therefrom methanol washs, dried that pure organic room temperature phosphorimetry gathers
Laminate material.
2. according to the preparation method of the pure organic room temperature phosphorimetry polymeric material described in claim 1, it is characterised in that described
In phosphorescent monomer in step (1), the position of heavy atom, number and kind do not limit, the length of the alkyl chain of the band olefinic double bonds connect
Not limiting, the solvent in step (2) is DMF or dimethyl sulfoxide, and initiator is not limited to azodiisobutyronitrile.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109306034A (en) * | 2018-03-16 | 2019-02-05 | 华东理工大学 | A kind of preparation method of pure organic long-life room temperature phosphorimetry polymer material of no heavy atom amorphous state |
| CN109957106A (en) * | 2019-03-13 | 2019-07-02 | 北京大学 | A kind of room temperature phosphorimetry nylon copolymer and preparation method thereof |
| CN112210037A (en) * | 2020-10-14 | 2021-01-12 | 南京邮电大学 | Organic phosphonate long-life room temperature phosphorescent polymer material and preparation and application thereof |
| CN115433427A (en) * | 2022-08-10 | 2022-12-06 | 华东理工大学 | Light-activated circular polarization phosphorescent material and preparation method and application thereof |
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| EP0605355A1 (en) * | 1992-12-30 | 1994-07-06 | Universidad De Oviedo | Oxygen-quenchable phosphorescent materials and their applications in oxygen sensing |
| WO2007061574A2 (en) * | 2005-11-22 | 2007-05-31 | Sca Research, Llc | Room temperature phosphorescence apparatus and methods |
| CN105199724A (en) * | 2015-10-10 | 2015-12-30 | 北京化工大学 | Carbon quantum dots with room-temperature phosphorescence and delayed fluorescence properties, and synthesis and application thereof |
| CN105237551A (en) * | 2015-10-09 | 2016-01-13 | 北京师范大学 | Zinc-based metal organic framework materials having room temperature phosphorescence characteristic and preparation method thereof |
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2016
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Patent Citations (4)
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| EP0605355A1 (en) * | 1992-12-30 | 1994-07-06 | Universidad De Oviedo | Oxygen-quenchable phosphorescent materials and their applications in oxygen sensing |
| WO2007061574A2 (en) * | 2005-11-22 | 2007-05-31 | Sca Research, Llc | Room temperature phosphorescence apparatus and methods |
| CN105237551A (en) * | 2015-10-09 | 2016-01-13 | 北京师范大学 | Zinc-based metal organic framework materials having room temperature phosphorescence characteristic and preparation method thereof |
| CN105199724A (en) * | 2015-10-10 | 2015-12-30 | 北京化工大学 | Carbon quantum dots with room-temperature phosphorescence and delayed fluorescence properties, and synthesis and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| HUI CHEN等: "Room temperature phosphorescence of 4-bromo 1,8-naphthalic anhydride derivative-based polyacrylamide copolymer with photo-stimulated responsiveness", 《POLYM. CHEM.》 * |
| MIN SANG KWON等: "Tailoring Intermolecular Interactions for Efficient Room-Temperature Phosphorescence from Purely Organic Materials in Amorphous Polymer Matrices", 《ANGEW. CHEM. INT . ED.》 * |
| 邬帅帆: "基于大环主体的功能性超分子组装体的合成及性能研究", 《中国博士学位论文全文数据库，工程科技Ⅰ辑》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109306034A (en) * | 2018-03-16 | 2019-02-05 | 华东理工大学 | A kind of preparation method of pure organic long-life room temperature phosphorimetry polymer material of no heavy atom amorphous state |
| CN109306034B (en) * | 2018-03-16 | 2023-03-03 | 华东理工大学 | Preparation method of pure organic long-life room-temperature phosphorescent polymer material in heavy-atom-free amorphous state |
| CN109957106A (en) * | 2019-03-13 | 2019-07-02 | 北京大学 | A kind of room temperature phosphorimetry nylon copolymer and preparation method thereof |
| CN112210037A (en) * | 2020-10-14 | 2021-01-12 | 南京邮电大学 | Organic phosphonate long-life room temperature phosphorescent polymer material and preparation and application thereof |
| CN115433427A (en) * | 2022-08-10 | 2022-12-06 | 华东理工大学 | Light-activated circular polarization phosphorescent material and preparation method and application thereof |
| CN115433427B (en) * | 2022-08-10 | 2024-01-26 | 华东理工大学 | Optically activated circularly polarized phosphorescent material, and preparation method and application thereof |
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